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Search results; 491 homes in Deal Island Historic District

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Cottage in Deal Island
Deal Island Bay Cottage - Maryland
3 bedrooms, 6 beds, 2 shared bathrooms
20–25 Sept
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4.63 out of 5 average rating, 273 reviews
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Guest favourite
Cottage in Deal Island
Water View Cottage
2 bedrooms, 3 beds
15–20 Oct
4.93 out of 5 average rating, 174 reviews
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Home in Deal Island
House of the Setting Sun/Deal Island Bayfront Home
3 bedrooms, 7 beds
17–22 Sept
4.85 out of 5 average rating, 46 reviews
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Guest favourite
Home in Deal Island
Rusty Anchor
3 bedrooms, 7 beds
18–23 Sept
4.94 out of 5 average rating, 51 reviews
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Top guest favourite
Home in Deal Island
The Tangier Escape
2 bedrooms, 3 beds
20–25 Sept
4.97 out of 5 average rating, 30 reviews
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Guest favourite
Guest suite in Deal Island
Private guest suite near Deal Island Maryland
1 bedroom, 2 double beds
17–22 Sept
4.88 out of 5 average rating, 136 reviews
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Cottage in Deal Island
Waterfront Maryland Retreat w/ Dock & Bay View!
3 bedrooms, 5 beds
18–23 Sept
4.88 out of 5 average rating, 17 reviews
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Top guest favourite
Cottage in Deal Island
Private Beachfront Cottage with 2 Bedrooms + Loft
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.94 out of 5 average rating, 100 reviews
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Top guest favourite
Home in Deal Island
Deal Island Lodge
4 bedrooms, 11 beds
20–25 Sept
5.0 out of 5 average rating, 37 reviews
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Top guest favourite
Cottage in Deal Island
Bayfront Bliss on Tangier Sound
1 bedroom, 3 beds
5–10 Oct
4.96 out of 5 average rating, 26 reviews
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Guest favourite
Home in Deal Island
Maryland Retreat: Walk to Bay, Beach & Boat Ramp!
4 bedrooms, 6 beds
27 Sept – 2 Oct
4.94 out of 5 average rating, 33 reviews
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Guest favourite
Home in Princess Anne
Ye Ole Pirate House
3 bedrooms, 4 beds
17–22 Sept
4.88 out of 5 average rating, 43 reviews
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Top guest favourite
Rooms in Nanticoke
A Piece of Paradise
2 bedrooms, 3 beds
20–25 Sept
4.97 out of 5 average rating, 231 reviews
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Home in Crisfield
Charming Crisfield Cottage
3 bedrooms, 3 double beds
27 Sept – 2 Oct
4.5 out of 5 average rating, 115 reviews
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Top guest favourite
Home in Crisfield
Cozy Crisfield Cottage
3 bedrooms, 5 beds
20–25 Sept
4.93 out of 5 average rating, 68 reviews
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Guest favourite
Home in Smith Island
Pelican Cove *Pet Friendly*Golf Cart*Boat Slip
2 bedrooms, 3 beds
28 Sept – 3 Oct
4.91 out of 5 average rating, 11 reviews
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Top guest favourite
Home in Deal Island
"Promise Point" Bay front home with dock. 3BR 2BA
3 bedrooms, 8 beds
22–27 Sept
4.94 out of 5 average rating, 84 reviews
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Home in Westover
Goose Creek Cottage: Secluded Waterfront Retreat
2 bedrooms, 6 beds
19–24 Sept
New place to stay
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Top guest favourite
Cottage in Westover
Rumbley Cottage on the Tangier Sound-Private Beach
2 bedrooms, 2 queen beds
15–20 Nov
4.99 out of 5 average rating, 266 reviews